# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rtp
_database_code_depnum_ccdc_archive 'CCDC 2111863'
loop_
_audit_author_name
_audit_author_address
'Wang Yan Ning '
;Jiang Su University of Science and Technology
China
;
_audit_update_record             
;
2021-09-25 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Cl4 Sb), 3(C10 H16 N), Cl'
_chemical_formula_sum            'C30 H48 Cl9 N3 Sb2'
_chemical_formula_weight         1013.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.2809(9)
_cell_length_b                   25.774(3)
_cell_length_c                   17.6172(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2610(10)
_cell_angle_gamma                90.00
_cell_volume                     4210.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      2.50
_exptl_absorpt_coefficient_mu    1.879
_exptl_absorpt_correction_T_max  0.8200
_exptl_absorpt_correction_T_min  0.7923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27639
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.40
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7095
_reflns_number_total             8251
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.010
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         8251
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0771P)²+19.0794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1524
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N2 \\sim C7AA \\sim C9AA \\sim C3AA \\sim C5: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C2AA(H2AA,H2AB), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C8AA(H8AA), C6(H6), C7(H7),
 C8(H8), C10(H10), C0AA(H0AA), C1AA(H1AA), C5AA(H5AA), C6AA(H6AA), C4AA(H4AA)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C3(H3A,H3B,
 H3C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C3AA(H3AA,H3AB,H3AC), C7AA(H7AA,
 H7AB,H7AC), C9AA(H9AA,H9AB,H9AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl2 Cl 0.2228(3) 0.64452(7) 0.71308(12) 0.0689(5) Uani 1 d . . . .
Sb1 Sb 0.22940(4) 0.560513(15) 0.77782(2) 0.03664(13) Uani 1 d . . . .
Sb2 Sb 0.27367(4) 0.422045(16) 0.68781(2) 0.03628(13) Uani 1 d . . . .
Cl3 Cl 0.20331(16) 0.45020(6) 0.84018(8) 0.0419(3) Uani 1 d . . . .
Cl5 Cl 0.01986(18) 0.53061(7) 0.67544(9) 0.0503(4) Uani 1 d . . . .
Cl6 Cl 0.43815(18) 0.59670(7) 0.87129(9) 0.0484(4) Uani 1 d . . . .
Cl7 Cl 0.34086(19) 0.40557(7) 0.55299(9) 0.0481(4) Uani 1 d . . . .
Cl8 Cl 0.47295(18) 0.37413(7) 0.73914(9) 0.0498(4) Uani 1 d . . . .
Cl9 Cl 0.1276(2) 0.34069(8) 0.68438(11) 0.0590(5) Uani 1 d . . . .
Cl10 Cl 0.0482(2) 0.58838(8) 0.86774(10) 0.0561(4) Uani 1 d . . . .
N0AA N 0.2067(6) 0.9210(2) 0.9576(3) 0.0427(12) Uani 1 d . . . .
C13 C 0.2430(7) 0.8228(3) 0.9688(4) 0.0446(14) Uani 1 d . . . .
C14 C 0.0489(7) 0.9204(3) 0.9704(4) 0.0536(17) Uani 1 d . . . .
H14A H 0.0045 0.9502 0.9467 0.080 Uiso 1 calc . . GR .
H14B H 0.0335 0.9211 1.0240 0.080 Uiso 1 calc . . GR .
H14C H 0.0070 0.8894 0.9488 0.080 Uiso 1 calc . . GR .
C15 C 0.2272(9) 0.9189(3) 0.8747(4) 0.0552(18) Uani 1 d . . . .
H15A H 0.1822 0.8882 0.8539 0.083 Uiso 1 calc . . GR .
H15B H 0.3284 0.9182 0.8654 0.083 Uiso 1 calc . . GR .
H15C H 0.1844 0.9490 0.8509 0.083 Uiso 1 calc . . GR .
C16 C 0.1770(13) 0.7262(4) 0.9114(7) 0.089(3) Uani 1 d . . . .
H16 H 0.1551 0.6936 0.8917 0.107 Uiso 1 calc . . R .
C17 C 0.1271(9) 0.7959(3) 0.9937(5) 0.068(2) Uani 1 d . . . .
H17 H 0.0709 0.8102 1.0309 0.081 Uiso 1 calc . . R .
C18 C 0.3271(10) 0.7998(3) 0.9153(5) 0.066(2) Uani 1 d . . . .
H18 H 0.4078 0.8172 0.8986 0.080 Uiso 1 calc . . R .
C19 C 0.2826(8) 0.8757(3) 0.9991(4) 0.0507(16) Uani 1 d . . . .
H19A H 0.3860 0.8803 0.9961 0.061 Uiso 1 calc . . R .
H19B H 0.2599 0.8771 1.0524 0.061 Uiso 1 calc . . R .
C20 C 0.0925(11) 0.7474(4) 0.9641(7) 0.090(3) Uani 1 d . . . .
H20 H 0.0120 0.7296 0.9802 0.107 Uiso 1 calc . . R .
C21 C 0.2943(14) 0.7526(4) 0.8869(6) 0.087(3) Uani 1 d . . . .
H21 H 0.3516 0.7378 0.8505 0.105 Uiso 1 calc . . R .
C22 C 0.2699(10) 0.9700(3) 0.9880(5) 0.070(2) Uani 1 d . . . .
H22A H 0.2144 0.9989 0.9687 0.105 Uiso 1 calc . . GR .
H22B H 0.3675 0.9731 0.9725 0.105 Uiso 1 calc . . GR .
H22C H 0.2687 0.9697 1.0424 0.105 Uiso 1 calc . . GR .
N1 N 0.2704(6) 0.5311(2) 0.0920(3) 0.0450(13) Uani 1 d . . . .
C2AA C 0.1773(8) 0.5762(3) 0.0651(4) 0.0569(19) Uani 1 d . . . .
H2AA H 0.1861 0.5800 0.0107 0.068 Uiso 1 calc . . R .
H2AB H 0.0774 0.5678 0.0740 0.068 Uiso 1 calc . . R .
C3 C 0.4272(7) 0.5426(3) 0.0838(5) 0.0590(19) Uani 1 d . . . .
H3A H 0.4440 0.5514 0.0319 0.088 Uiso 1 calc . . GR .
H3B H 0.4832 0.5127 0.0982 0.088 Uiso 1 calc . . GR .
H3C H 0.4548 0.5713 0.1160 0.088 Uiso 1 calc . . GR .
C4 C 0.2123(7) 0.6270(3) 0.1021(4) 0.0500(16) Uani 1 d . . . .
C8AA C 0.1765(9) 0.6897(4) 0.2003(5) 0.071(2) Uani 1 d . . . .
H8AA H 0.1311 0.6997 0.2441 0.086 Uiso 1 calc . . R .
C6 C 0.3426(12) 0.7067(4) 0.1045(6) 0.079(3) Uani 1 d . . . .
H6 H 0.4101 0.7284 0.0832 0.095 Uiso 1 calc . . R .
C7 C 0.1434(8) 0.6425(3) 0.1665(5) 0.063(2) Uani 1 d . . . .
H7 H 0.0745 0.6212 0.1873 0.075 Uiso 1 calc . . R .
C8 C 0.2752(11) 0.7216(4) 0.1696(6) 0.078(3) Uani 1 d . . . .
H8 H 0.2973 0.7534 0.1923 0.094 Uiso 1 calc . . R .
C9 C 0.2446(11) 0.5182(4) 0.1735(4) 0.070(2) Uani 1 d . . . .
H9A H 0.2703 0.5474 0.2050 0.105 Uiso 1 calc . . GR .
H9B H 0.3025 0.4889 0.1887 0.105 Uiso 1 calc . . GR .
H9C H 0.1446 0.5101 0.1788 0.105 Uiso 1 calc . . GR .
C10 C 0.3099(10) 0.6597(3) 0.0713(5) 0.067(2) Uani 1 d . . . .
H10 H 0.3548 0.6501 0.0271 0.081 Uiso 1 calc . . R .
C11 C 0.2318(10) 0.4843(3) 0.0449(5) 0.068(2) Uani 1 d . . . .
H11A H 0.1328 0.4753 0.0518 0.102 Uiso 1 calc . . GR .
H11B H 0.2926 0.4558 0.0605 0.102 Uiso 1 calc . . GR .
H11C H 0.2453 0.4918 -0.0077 0.102 Uiso 1 calc . . GR .
Cl1 Cl 0.45815(16) 0.51372(6) 0.68103(8) 0.0420(3) Uani 1 d . . . .
N2 N 0.7254(9) 0.6813(4) 0.7073(6) 0.095(2) Uani 1 d . . . U
C1 C 0.7786(9) 0.7408(3) 0.5973(5) 0.062(2) Uani 1 d . . . .
C0AA C 0.7353(11) 0.7229(4) 0.5272(5) 0.078(3) Uani 1 d . . . .
H0AA H 0.7375 0.6874 0.5176 0.093 Uiso 1 calc . . R .
C1AA C 0.7690(13) 0.7943(4) 0.6097(6) 0.091(3) Uani 1 d . . . .
H1AA H 0.7924 0.8081 0.6574 0.109 Uiso 1 calc . . R .
C3AA C 0.6316(13) 0.7199(5) 0.7416(7) 0.110(4) Uani 1 d . . . U
H3AA H 0.6896 0.7468 0.7649 0.164 Uiso 1 calc . . GR .
H3AB H 0.5755 0.7034 0.7793 0.164 Uiso 1 calc . . GR .
H3AC H 0.5684 0.7347 0.7030 0.164 Uiso 1 calc . . GR .
C5 C 0.8341(10) 0.7071(5) 0.6610(7) 0.102(3) Uani 1 d . . . U
H5A H 0.8944 0.6805 0.6398 0.122 Uiso 1 calc . . R .
H5B H 0.8953 0.7281 0.6946 0.122 Uiso 1 calc . . R .
C5AA C 0.6814(15) 0.8057(6) 0.4830(7) 0.111(4) Uani 1 d . . . .
H5AA H 0.6456 0.8272 0.4442 0.134 Uiso 1 calc . . R .
C6AA C 0.6894(12) 0.7555(6) 0.4714(6) 0.097(4) Uani 1 d . . . .
H6AA H 0.6629 0.7421 0.4238 0.117 Uiso 1 calc . . R .
C4AA C 0.7244(15) 0.8268(4) 0.5503(7) 0.102(4) Uani 1 d . . . .
H4AA H 0.7242 0.8626 0.5568 0.122 Uiso 1 calc . . R .
C7AA C 0.625(2) 0.6484(6) 0.6604(9) 0.151(5) Uani 1 d . . . U
H7AA H 0.5571 0.6321 0.6926 0.226 Uiso 1 calc . . GR .
H7AB H 0.6786 0.6223 0.6349 0.226 Uiso 1 calc . . GR .
H7AC H 0.5739 0.6696 0.6234 0.226 Uiso 1 calc . . GR .
C9AA C 0.7934(17) 0.6531(7) 0.7728(9) 0.162(6) Uani 1 d . . . U
H9AA H 0.8563 0.6761 0.8013 0.242 Uiso 1 calc . . GR .
H9AB H 0.8481 0.6243 0.7546 0.242 Uiso 1 calc . . GR .
H9AC H 0.7198 0.6405 0.8049 0.242 Uiso 1 calc . . GR .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 Sb1 2.4469(18) . ?
Sb1 Cl5 2.7116(15) . ?
Sb1 Cl6 2.6614(15) . ?
Sb1 Cl10 2.4626(18) . ?
Sb2 Cl3 2.8806(15) . ?
Sb2 Cl7 2.5154(16) . ?
Sb2 Cl8 2.3730(16) . ?
Sb2 Cl9 2.4964(18) . ?
N0AA C14 1.491(8) . ?
N0AA C15 1.483(8) . ?
N0AA C19 1.533(9) . ?
N0AA C22 1.484(9) . ?
C13 C17 1.367(10) . ?
C13 C18 1.381(10) . ?
C13 C19 1.505(10) . ?
C16 C20 1.353(15) . ?
C16 C21 1.367(15) . ?
C17 C20 1.387(14) . ?
C18 C21 1.346(13) . ?
N1 C2AA 1.512(9) . ?
N1 C3 1.497(9) . ?
N1 C9 1.502(8) . ?
N1 C11 1.500(9) . ?
C2AA C4 1.493(11) . ?
C4 C7 1.384(11) . ?
C4 C10 1.367(11) . ?
C8AA C7 1.383(12) . ?
C8AA C8 1.359(14) . ?
C6 C8 1.383(14) . ?
C6 C10 1.373(13) . ?
N2 C3AA 1.467(14) . ?
N2 C5 1.479(13) . ?
N2 C7AA 1.488(18) . ?
N2 C9AA 1.484(15) . ?
C1 C0AA 1.365(12) . ?
C1 C1AA 1.400(14) . ?
C1 C5 1.494(13) . ?
C0AA C6AA 1.349(15) . ?
C1AA C4AA 1.389(16) . ?
C5AA C6AA 1.314(17) . ?
C5AA C4AA 1.349(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Sb1 Cl5 86.41(7) . . ?
Cl2 Sb1 Cl6 89.00(7) . . ?
Cl2 Sb1 Cl10 92.10(7) . . ?
Cl6 Sb1 Cl5 175.31(6) . . ?
Cl10 Sb1 Cl5 91.18(6) . . ?
Cl10 Sb1 Cl6 89.93(6) . . ?
Cl7 Sb2 Cl3 175.02(5) . . ?
Cl8 Sb2 Cl3 88.74(5) . . ?
Cl8 Sb2 Cl7 93.07(6) . . ?
Cl8 Sb2 Cl9 89.23(6) . . ?
Cl9 Sb2 Cl3 95.24(6) . . ?
Cl9 Sb2 Cl7 89.43(6) . . ?
C14 N0AA C19 110.8(6) . . ?
C15 N0AA C14 108.3(6) . . ?
C15 N0AA C19 111.6(5) . . ?
C15 N0AA C22 108.7(6) . . ?
C22 N0AA C14 109.4(6) . . ?
C22 N0AA C19 107.9(6) . . ?
C17 C13 C18 118.3(8) . . ?
C17 C13 C19 122.0(7) . . ?
C18 C13 C19 119.7(7) . . ?
C20 C16 C21 120.5(10) . . ?
C13 C17 C20 120.7(9) . . ?
C21 C18 C13 121.1(9) . . ?
C13 C19 N0AA 114.7(5) . . ?
C16 C20 C17 119.3(10) . . ?
C18 C21 C16 120.2(10) . . ?
C3 N1 C2AA 111.3(6) . . ?
C3 N1 C9 109.2(6) . . ?
C3 N1 C11 108.6(6) . . ?
C9 N1 C2AA 111.0(6) . . ?
C11 N1 C2AA 108.9(6) . . ?
C11 N1 C9 107.8(6) . . ?
C4 C2AA N1 115.1(5) . . ?
C7 C4 C2AA 120.8(7) . . ?
C10 C4 C2AA 120.3(7) . . ?
C10 C4 C7 118.8(8) . . ?
C8 C8AA C7 120.2(9) . . ?
C10 C6 C8 120.0(9) . . ?
C8AA C7 C4 120.4(8) . . ?
C8AA C8 C6 119.7(9) . . ?
C4 C10 C6 120.9(9) . . ?
C3AA N2 C5 110.6(10) . . ?
C3AA N2 C7AA 104.2(10) . . ?
C3AA N2 C9AA 104.6(11) . . ?
C5 N2 C7AA 112.1(11) . . ?
C5 N2 C9AA 111.8(9) . . ?
C9AA N2 C7AA 112.9(12) . . ?
C0AA C1 C1AA 117.1(9) . . ?
C0AA C1 C5 124.3(10) . . ?
C1AA C1 C5 118.6(10) . . ?
C6AA C0AA C1 121.6(10) . . ?
C4AA C1AA C1 119.6(9) . . ?
N2 C5 C1 116.9(8) . . ?
C6AA C5AA C4AA 121.1(11) . . ?
C5AA C6AA C0AA 121.1(10) . . ?
C5AA C4AA C1AA 119.3(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HCl'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2111864'
loop_
_audit_author_name
_audit_author_address
'Wang Yan Ning '
;Jiang Su University of Science and Technology
China
;
_audit_update_record             
;
2021-09-25 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2021-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl4 Sb, Cl3 Sb, 3(C10 H15 F N), 2(Cl)'
_chemical_formula_sum            'C30 H45 Cl9 F3 N3 Sb2'
_chemical_formula_weight         1067.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.275(2)
_cell_length_b                   13.826(3)
_cell_length_c                   18.274(4)
_cell_angle_alpha                83.423(5)
_cell_angle_beta                 89.796(6)
_cell_angle_gamma                76.621(5)
_cell_volume                     2264.1(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      2.50
_exptl_absorpt_coefficient_mu    1.760
_exptl_absorpt_correction_T_max  0.8299
_exptl_absorpt_correction_T_min  0.8035
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16879
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.12
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6739
_reflns_number_total             9192
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.544
_refine_diff_density_min         -1.343
_refine_diff_density_rms         0.236
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         9192
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0898
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1772P)²+17.5220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2772
_refine_ls_wR_factor_ref         0.3029
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.12
3. Uiso/Uaniso restraints and constraints
Uanis(N17) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C77) \\sim Ueq: with sigma of 0.006 and sigma for terminal
atoms of 0.012
4.a Secondary CH2 refined with riding coordinates:
 C77(H77A,H77B), C15(H15A,H15B), C10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C48(H48), C54(H54), C64(H64), C12(H12), C31(H31), C44(H44), C79(H79),
 C20(H20), C28(H28), C30(H30), C36(H36), C2(H2)
4.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C43(H43A,H43B,H43C), C11(H11A,H11B,H11C), C27(H27A,H27B,
 H27C), C33(H33A,H33B,H33C), C26(H26A,H26B,H26C), C49(H49A,H49B,H49C), C1(H1A,
 H1B,H1C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Sb1 Sb 0.80450(8) 0.37421(5) 0.31016(4) 0.0463(3) Uani 1 d . . . U
Sb2 Sb 0.67451(8) 0.62860(5) 0.19922(4) 0.0491(3) Uani 1 d . . . U
Cl6 Cl 1.0528(3) 0.2578(2) 0.30460(18) 0.0607(7) Uani 1 d . . . U
Cl7 Cl 0.6752(4) 0.2367(2) 0.31450(19) 0.0629(8) Uani 1 d . . . U
Cl8 Cl 0.4442(4) 0.6772(3) 0.11825(19) 0.0727(9) Uani 1 d . . . U
Cl9 Cl 0.8180(4) 0.6942(3) 0.10204(19) 0.0766(10) Uani 1 d . . . U
Cl10 Cl 0.8291(4) 0.3475(3) 0.45517(19) 0.0798(11) Uani 1 d . . . U
N17 N 1.1064(15) -0.1656(10) 0.2549(8) 0.081(3) Uani 1 d . . . U
C38 C 0.996(3) 0.1372(18) 0.0569(16) 0.121(6) Uani 1 d . . . U
C41 C 0.964(2) -0.1270(15) 0.2891(11) 0.103(5) Uani 1 d . . . U
H41A H 0.9018 -0.0773 0.2547 0.155 Uiso 1 calc . . GR .
H41B H 0.9816 -0.0974 0.3323 0.155 Uiso 1 calc . . GR .
H41C H 0.9167 -0.1809 0.3026 0.155 Uiso 1 calc . . GR .
C43 C 1.070(2) -0.2084(16) 0.1870(11) 0.106(6) Uani 1 d . . . U
H43A H 1.0677 -0.2775 0.1997 0.159 Uiso 1 calc . . GR .
H43B H 1.1434 -0.2035 0.1507 0.159 Uiso 1 calc . . GR .
H43C H 0.9742 -0.1717 0.1675 0.159 Uiso 1 calc . . GR .
C48 C 1.012(3) 0.0735(16) 0.1843(13) 0.121(7) Uani 1 d . . . U
H48 H 0.9845 0.0835 0.2324 0.145 Uiso 1 calc . . R .
F53 F 0.939(2) 0.2049(11) -0.0010(10) 0.162(6) Uani 1 d . . . U
C54 C 1.164(2) -0.008(2) 0.1058(16) 0.122(7) Uani 1 d . . . U
H54 H 1.2423 -0.0610 0.0980 0.147 Uiso 1 calc . . R .
C64 C 0.937(4) 0.1490(17) 0.1248(16) 0.155(11) Uani 1 d . . . U
H64 H 0.8558 0.2004 0.1328 0.186 Uiso 1 calc . . R .
C73 C 1.111(2) -0.0035(13) 0.1756(12) 0.092(4) Uani 1 d . . . U
C77 C 1.179(2) -0.0765(16) 0.2348(12) 0.105(5) Uani 1 d . . . U
H77A H 1.1802 -0.0427 0.2784 0.126 Uiso 1 calc . . R .
H77B H 1.2810 -0.1030 0.2224 0.126 Uiso 1 calc . . R .
N4 N 0.2915(10) 0.3607(7) 0.4816(5) 0.049(2) Uani 1 d . . . U
C11 C 0.4272(16) 0.3933(12) 0.5051(10) 0.080(4) Uani 1 d . . . U
H11A H 0.4937 0.3380 0.5330 0.121 Uiso 1 calc . . GR .
H11B H 0.3980 0.4471 0.5349 0.121 Uiso 1 calc . . GR .
H11C H 0.4760 0.4157 0.4622 0.121 Uiso 1 calc . . GR .
C12 C 0.337(2) 0.1143(11) 0.5464(9) 0.079(4) Uani 1 d . . . U
H12 H 0.2341 0.1284 0.5405 0.094 Uiso 1 calc . . R .
C13 C 0.4141(16) 0.1759(10) 0.5087(7) 0.061(3) Uani 1 d . . . U
C15 C 0.3398(16) 0.2598(10) 0.4537(7) 0.063(3) Uani 1 d . . . U
H15A H 0.2532 0.2429 0.4338 0.076 Uiso 1 calc . . R .
H15B H 0.4069 0.2657 0.4134 0.076 Uiso 1 calc . . R .
F21 F 0.6182(16) -0.0665(8) 0.6516(6) 0.129(5) Uani 1 d . . . U
C27 C 0.1889(16) 0.3581(12) 0.5447(8) 0.077(4) Uani 1 d . . . U
H27A H 0.2286 0.3008 0.5797 0.115 Uiso 1 calc . . GR .
H27B H 0.0936 0.3538 0.5268 0.115 Uiso 1 calc . . GR .
H27C H 0.1785 0.4179 0.5681 0.115 Uiso 1 calc . . GR .
C31 C 0.5630(16) 0.1550(12) 0.5196(8) 0.071(3) Uani 1 d . . . U
H31 H 0.6186 0.1954 0.4942 0.085 Uiso 1 calc . . R .
C33 C 0.2083(19) 0.4358(10) 0.4236(8) 0.080(4) Uani 1 d . . . U
H33A H 0.1541 0.4928 0.4455 0.120 Uiso 1 calc . . GR .
H33B H 0.1404 0.4070 0.3987 0.120 Uiso 1 calc . . GR .
H33C H 0.2763 0.4564 0.3888 0.120 Uiso 1 calc . . GR .
C44 C 0.406(2) 0.0334(12) 0.5923(9) 0.086(4) Uani 1 d . . . U
H44 H 0.3519 -0.0101 0.6148 0.103 Uiso 1 calc . . R .
C47 C 0.550(2) 0.0155(12) 0.6053(8) 0.086(4) Uani 1 d . . . U
C79 C 0.6332(19) 0.0728(13) 0.5688(8) 0.082(4) Uani 1 d . . . U
H79 H 0.7354 0.0578 0.5762 0.099 Uiso 1 calc . . R .
N5 N 0.2747(12) 0.4053(8) 0.1150(6) 0.060(2) Uani 1 d . . . U
C9 C 0.3578(15) 0.2173(10) 0.1135(7) 0.062(3) Uani 1 d . . . U
C10 C 0.2322(16) 0.3056(11) 0.1083(8) 0.069(3) Uani 1 d . . . U
H10A H 0.1634 0.2950 0.1468 0.083 Uiso 1 calc . . R .
H10B H 0.1808 0.3109 0.0613 0.083 Uiso 1 calc . . R .
F14 F 0.7086(16) -0.0301(9) 0.1286(7) 0.152(6) Uani 1 d . . . U
C20 C 0.401(2) 0.1589(12) 0.1805(8) 0.080(4) Uani 1 d . . . U
H20 H 0.3515 0.1774 0.2229 0.096 Uiso 1 calc . . R .
C26 C 0.385(2) 0.4220(13) 0.0565(10) 0.093(5) Uani 1 d . . . U
H26A H 0.4664 0.3645 0.0594 0.140 Uiso 1 calc . . GR .
H26B H 0.4200 0.4801 0.0641 0.140 Uiso 1 calc . . GR .
H26C H 0.3371 0.4318 0.0087 0.140 Uiso 1 calc . . GR .
C28 C 0.436(2) 0.1917(13) 0.0524(8) 0.095(6) Uani 1 d . . . U
H28 H 0.4142 0.2329 0.0080 0.114 Uiso 1 calc . . R .
C30 C 0.548(2) 0.1044(14) 0.0557(10) 0.112(7) Uani 1 d . . . U
H30 H 0.5955 0.0839 0.0132 0.135 Uiso 1 calc . . R .
C36 C 0.512(2) 0.0773(14) 0.1857(9) 0.100(6) Uani 1 d . . . U
H36 H 0.5381 0.0393 0.2310 0.120 Uiso 1 calc . . R .
C49 C 0.339(2) 0.4042(15) 0.1900(9) 0.094(5) Uani 1 d . . . U
H49A H 0.2801 0.3759 0.2262 0.141 Uiso 1 calc . . GR .
H49B H 0.3380 0.4714 0.1988 0.141 Uiso 1 calc . . GR .
H49C H 0.4385 0.3646 0.1931 0.141 Uiso 1 calc . . GR .
C63 C 0.588(2) 0.0495(12) 0.1229(9) 0.092(5) Uani 1 d . . . U
Cl1 Cl 0.6042(4) 0.7845(2) 0.2587(2) 0.0734(9) Uani 1 d . . . U
Cl2 Cl 0.7689(3) 0.41307(19) 0.15229(14) 0.0455(6) Uani 1 d . . . U
Cl11 Cl 0.5180(3) 0.5207(2) 0.31713(14) 0.0517(6) Uani 1 d . . . U
C1 C 0.1402(18) 0.4865(14) 0.0987(11) 0.095(5) Uani 1 d . . . U
H1A H 0.1075 0.4878 0.0487 0.142 Uiso 1 calc . . GR .
H1B H 0.1623 0.5495 0.1052 0.142 Uiso 1 calc . . GR .
H1C H 0.0633 0.4749 0.1315 0.142 Uiso 1 calc . . GR .
C2 C 1.109(3) 0.062(2) 0.0458(16) 0.125(7) Uani 1 d . . . U
H2 H 1.1500 0.0566 -0.0005 0.150 Uiso 1 calc . . R .
C19 C 1.195(3) -0.241(2) 0.3100(15) 0.145(8) Uani 1 d . . . U
H19A H 1.1730 -0.2219 0.3583 0.218 Uiso 1 calc . . GR .
H19B H 1.2984 -0.2467 0.3010 0.218 Uiso 1 calc . . GR .
H19C H 1.1715 -0.3047 0.3066 0.218 Uiso 1 calc . . GR .
Cl3 Cl 0.9495(3) 0.56421(19) 0.28882(12) 0.0425(5) Uani 1 d . . . U


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl6 2.495(3) . ?
Sb1 Cl7 2.466(3) . ?
Sb1 Cl10 2.637(4) . ?
Sb1 Cl2 2.879(3) . ?
Sb2 Cl8 2.516(3) . ?
Sb2 Cl9 2.433(3) . ?
Sb2 Cl1 2.476(3) . ?
N17 C41 1.47(2) . ?
N17 C43 1.51(2) . ?
N17 C77 1.54(2) . ?
N17 C19 1.47(3) . ?
C38 F53 1.35(3) . ?
C38 C64 1.37(3) . ?
C38 C2 1.33(3) . ?
C48 C64 1.47(4) . ?
C48 C73 1.26(3) . ?
C54 C73 1.37(3) . ?
C54 C2 1.39(3) . ?
C73 C77 1.43(3) . ?
N4 C11 1.510(15) . ?
N4 C15 1.509(15) . ?
N4 C27 1.495(15) . ?
N4 C33 1.477(16) . ?
C12 C13 1.36(2) . ?
C12 C44 1.35(2) . ?
C13 C15 1.483(19) . ?
C13 C31 1.35(2) . ?
F21 C47 1.361(18) . ?
C31 C79 1.40(2) . ?
C44 C47 1.32(2) . ?
C47 C79 1.35(2) . ?
N5 C10 1.536(17) . ?
N5 C26 1.510(18) . ?
N5 C49 1.492(18) . ?
N5 C1 1.477(19) . ?
C9 C10 1.474(19) . ?
C9 C20 1.393(19) . ?
C9 C28 1.37(2) . ?
F14 C63 1.371(19) . ?
C20 C36 1.33(2) . ?
C28 C30 1.40(2) . ?
C30 C63 1.37(2) . ?
C36 C63 1.39(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl6 Sb1 Cl10 89.08(12) . . ?
Cl6 Sb1 Cl2 93.35(9) . . ?
Cl7 Sb1 Cl6 92.47(11) . . ?
Cl7 Sb1 Cl10 89.57(12) . . ?
Cl7 Sb1 Cl2 91.72(10) . . ?
Cl10 Sb1 Cl2 177.19(11) . . ?
Cl9 Sb2 Cl8 91.22(12) . . ?
Cl9 Sb2 Cl1 96.01(14) . . ?
Cl1 Sb2 Cl8 92.02(13) . . ?
C41 N17 C43 106.1(15) . . ?
C41 N17 C77 107.4(14) . . ?
C41 N17 C19 106.4(16) . . ?
C43 N17 C77 111.3(15) . . ?
C19 N17 C43 113.0(17) . . ?
C19 N17 C77 112.0(16) . . ?
F53 C38 C64 119(3) . . ?
C2 C38 F53 118(3) . . ?
C2 C38 C64 123(3) . . ?
C73 C48 C64 125(2) . . ?
C73 C54 C2 124(2) . . ?
C38 C64 C48 114(3) . . ?
C48 C73 C54 115(2) . . ?
C48 C73 C77 124(2) . . ?
C54 C73 C77 120(2) . . ?
C73 C77 N17 116.8(16) . . ?
C15 N4 C11 108.9(10) . . ?
C27 N4 C11 109.9(11) . . ?
C27 N4 C15 111.8(10) . . ?
C33 N4 C11 109.5(11) . . ?
C33 N4 C15 110.7(10) . . ?
C33 N4 C27 105.9(11) . . ?
C44 C12 C13 121.3(17) . . ?
C12 C13 C15 121.4(14) . . ?
C31 C13 C12 118.1(14) . . ?
C31 C13 C15 120.4(13) . . ?
C13 C15 N4 115.9(9) . . ?
C13 C31 C79 120.1(15) . . ?
C47 C44 C12 120.5(16) . . ?
C44 C47 F21 119.6(18) . . ?
C44 C47 C79 120.8(15) . . ?
C79 C47 F21 119.4(18) . . ?
C47 C79 C31 119.0(16) . . ?
C26 N5 C10 109.3(10) . . ?
C49 N5 C10 110.0(12) . . ?
C49 N5 C26 110.7(13) . . ?
C1 N5 C10 107.8(11) . . ?
C1 N5 C26 106.6(13) . . ?
C1 N5 C49 112.3(12) . . ?
C20 C9 C10 121.3(13) . . ?
C28 C9 C10 120.4(13) . . ?
C28 C9 C20 118.3(14) . . ?
C9 C10 N5 114.9(11) . . ?
C36 C20 C9 121.9(14) . . ?
C9 C28 C30 120.8(14) . . ?
C63 C30 C28 118.6(15) . . ?
C20 C36 C63 119.5(15) . . ?
F14 C63 C36 119.9(15) . . ?
C30 C63 F14 119.5(16) . . ?
C30 C63 C36 120.5(16) . . ?
C38 C2 C54 118(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HCl'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2111865'
loop_
_audit_author_name
_audit_author_address
'Wang Yan Ning '
;Jiang Su University of Science and Technology
China
;
_audit_update_record             
;
2021-09-25 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2021-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Cl4 Sb), Cl, 3(C10 H15 Cl N)'
_chemical_formula_sum            'C30 H45 Cl12 N3 Sb2'
_chemical_formula_weight         1116.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.1074(10)
_cell_length_b                   14.2404(16)
_cell_length_c                   18.540(2)
_cell_angle_alpha                84.512(9)
_cell_angle_beta                 89.419(9)
_cell_angle_gamma                77.186(8)
_cell_volume                     2333.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.53
_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_T_max  0.8208
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.1319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15117
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.99
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4782
_reflns_number_total             8736
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.696
_refine_diff_density_min         -1.891
_refine_diff_density_rms         0.210
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0995
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1668P)²+4.1889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2704
_refine_ls_wR_factor_ref         0.3082
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C70(H70A,H70B), C76(H76A,H76B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C29(H29), C41(H41), C42(H42), C46(H46),
 C54(H54), C8(H8), C44(H44), C52(H52), C4(H4)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C34(H34A,H34B,H34C), C50(H50A,H50B,H50C), C67(H67A,H67B,H67C), C81(H81A,
 H81B,H81C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Sb1 Sb 0.80610(10) 0.86461(6) 0.31217(5) 0.0518(3) Uani 1 d . . .
Sb2 Sb 0.67864(11) 1.10969(6) 0.20329(5) 0.0531(3) Uani 1 d . . .
Cl3 Cl 0.9458(4) 1.0496(3) 0.2875(2) 0.0589(9) Uani 1 d . . .
Cl4 Cl 0.5169(4) 1.0111(3) 0.3177(2) 0.0643(10) Uani 1 d . . .
Cl5 Cl 0.7797(4) 0.8908(3) 0.1666(2) 0.0655(10) Uani 1 d . . .
Cl6 Cl 0.8295(5) 1.1726(3) 0.1075(2) 0.0729(11) Uani 1 d . . .
Cl7 Cl 1.0552(4) 0.7587(3) 0.3019(2) 0.0752(12) Uani 1 d . . .
Cl8 Cl 0.6773(5) 0.7310(3) 0.3158(2) 0.0777(12) Uani 1 d . . .
Cl9 Cl 0.6123(5) 1.2588(3) 0.2627(2) 0.0756(12) Uani 1 d . . .
Cl10 Cl 0.8359(5) 0.8349(4) 0.4584(2) 0.0832(13) Uani 1 d . . .
Cl11 Cl 0.4493(5) 1.1601(3) 0.1212(2) 0.0790(12) Uani 1 d . . .
Cl1 Cl 1.3433(8) 0.5672(3) 0.3507(3) 0.114(2) Uani 1 d . . .
Cl2 Cl 0.6993(7) 1.4389(4) 0.1146(3) 0.1109(19) Uani 1 d . . .
N7 N 1.7164(12) 0.1332(7) 0.5159(6) 0.051(3) Uani 1 d . . .
N11 N 0.2796(13) 1.8998(9) 0.1130(7) 0.060(3) Uani 1 d . . .
C12 C 1.441(2) 0.3329(11) 0.4915(9) 0.067(4) Uani 1 d . . .
H12 H 1.3884 0.2949 0.5202 0.080 Uiso 1 calc . . R
C15 C 0.420(2) 1.6923(14) 0.0440(9) 0.091(6) Uani 1 d . . .
H15 H 0.3975 1.7314 0.0007 0.110 Uiso 1 calc . . R
C17 C 1.804(2) 0.0597(10) 0.5737(9) 0.075(5) Uani 1 d . . .
H17A H 1.8566 0.0920 0.6047 0.112 Uiso 1 calc . . GR
H17B H 1.8756 0.0117 0.5509 0.112 Uiso 1 calc . . GR
H17C H 1.7359 0.0292 0.6020 0.112 Uiso 1 calc . . GR
C18 C 1.6789(18) 0.2295(9) 0.5447(8) 0.058(4) Uani 1 d . . .
H18A H 1.7722 0.2457 0.5583 0.069 Uiso 1 calc . . R
H18B H 1.6209 0.2241 0.5884 0.069 Uiso 1 calc . . R
C19 C 0.3529(18) 1.7188(11) 0.1059(10) 0.070(4) Uani 1 d . . .
C20 C 1.5929(19) 0.3113(9) 0.4948(8) 0.062(4) Uani 1 d . . .
C23 C 1.8155(19) 0.1366(11) 0.4517(9) 0.072(5) Uani 1 d . . .
H23A H 1.9058 0.1550 0.4654 0.108 Uiso 1 calc . . GR
H23B H 1.7635 0.1830 0.4144 0.108 Uiso 1 calc . . GR
H23C H 1.8412 0.0739 0.4340 0.108 Uiso 1 calc . . GR
C24 C 1.602(2) 0.4464(11) 0.4080(9) 0.077(5) Uani 1 d . . .
H24 H 1.6547 0.4837 0.3786 0.093 Uiso 1 calc . . R
C29 C 0.496(3) 1.5786(15) 0.1721(12) 0.106(7) Uani 1 d . . .
H29 H 0.5194 1.5409 0.2160 0.127 Uiso 1 calc . . R
C30 C 1.441(3) 0.4667(11) 0.4040(9) 0.085(6) Uani 1 d . . .
C31 C 0.394(2) 1.9124(16) 0.0629(11) 0.100(6) Uani 1 d . . .
H31A H 0.4328 1.9671 0.0734 0.150 Uiso 1 calc . . GR
H31B H 0.3529 1.9231 0.0146 0.150 Uiso 1 calc . . GR
H31C H 0.4740 1.8554 0.0669 0.150 Uiso 1 calc . . GR
C32 C 0.347(3) 1.8956(15) 0.1882(11) 0.100(6) Uani 1 d . . .
H32A H 0.4524 1.8672 0.1876 0.150 Uiso 1 calc . . GR
H32B H 0.2979 1.8572 0.2219 0.150 Uiso 1 calc . . GR
H32C H 0.3315 1.9599 0.2028 0.150 Uiso 1 calc . . GR
C34 C 1.5795(18) 0.1008(11) 0.4930(10) 0.075(5) Uani 1 d . . .
H34A H 1.6079 0.0529 0.4593 0.113 Uiso 1 calc . . GR
H34B H 1.5079 0.1552 0.4704 0.113 Uiso 1 calc . . GR
H34C H 1.5349 0.0734 0.5348 0.113 Uiso 1 calc . . GR
C38 C 0.572(2) 1.5516(11) 0.1121(9) 0.073(5) Uani 1 d . . .
C41 C 1.6768(19) 0.3722(10) 0.4549(9) 0.068(4) Uani 1 d . . .
H41 H 1.7807 0.3614 0.4608 0.082 Uiso 1 calc . . R
C42 C 0.526(2) 1.6038(12) 0.0469(9) 0.074(5) Uani 1 d . . .
H42 H 0.5654 1.5801 0.0040 0.089 Uiso 1 calc . . R
C46 C 1.364(2) 0.4095(13) 0.4469(11) 0.087(5) Uani 1 d . . .
H46 H 1.2591 0.4231 0.4454 0.105 Uiso 1 calc . . R
C54 C 0.386(3) 1.6601(16) 0.1690(13) 0.112(8) Uani 1 d . . .
H54 H 0.3311 1.6764 0.2105 0.135 Uiso 1 calc . . R
C70 C 0.227(2) 1.8104(11) 0.1001(10) 0.075(5) Uani 1 d . . .
H70A H 0.1815 1.8190 0.0522 0.090 Uiso 1 calc . . R
H70B H 0.1501 1.8019 0.1351 0.090 Uiso 1 calc . . R
Cl12 Cl 0.9270(11) 0.7008(5) 0.0190(4) 0.153(3) Uani 1 d . . .
C8 C 1.175(2) 0.4646(18) 0.1216(18) 0.111(8) Uani 1 d . . .
H8 H 1.2535 0.4153 0.1084 0.133 Uiso 1 calc . . R
N14 N 1.1088(16) 0.3107(10) 0.2655(9) 0.080(4) Uani 1 d . . .
C26 C 1.129(2) 0.4647(14) 0.1911(15) 0.096(7) Uani 1 d . . .
C35 C 1.010(3) 0.6091(17) 0.0836(14) 0.111(8) Uani 1 d . . .
C44 C 1.106(3) 0.538(2) 0.0691(15) 0.113(8) Uani 1 d . . .
H44 H 1.1345 0.5332 0.0210 0.136 Uiso 1 calc . . R
C50 C 0.952(2) 0.3444(18) 0.2927(14) 0.119(8) Uani 1 d . . .
H50A H 0.9042 0.2904 0.3000 0.179 Uiso 1 calc . . GR
H50B H 0.8946 0.3923 0.2577 0.179 Uiso 1 calc . . GR
H50C H 0.9557 0.3718 0.3378 0.179 Uiso 1 calc . . GR
C52 C 0.958(4) 0.6185(14) 0.1552(15) 0.135(10) Uani 1 d . . .
H52 H 0.8827 0.6701 0.1671 0.162 Uiso 1 calc . . R
C67 C 1.200(3) 0.231(2) 0.3175(19) 0.168(13) Uani 1 d . . .
H67A H 1.2362 0.2583 0.3572 0.252 Uiso 1 calc . . GR
H67B H 1.2842 0.1951 0.2925 0.252 Uiso 1 calc . . GR
H67C H 1.1377 0.1876 0.3358 0.252 Uiso 1 calc . . GR
C76 C 1.195(2) 0.3855(15) 0.2524(14) 0.110(7) Uani 1 d . . .
H76A H 1.2973 0.3553 0.2403 0.132 Uiso 1 calc . . R
H76B H 1.1992 0.4159 0.2968 0.132 Uiso 1 calc . . R
C81 C 1.096(3) 0.2633(16) 0.1943(12) 0.118(8) Uani 1 d . . .
H81A H 1.0250 0.2228 0.2005 0.177 Uiso 1 calc . . GR
H81B H 1.1931 0.2248 0.1831 0.177 Uiso 1 calc . . GR
H81C H 1.0637 0.3128 0.1554 0.177 Uiso 1 calc . . GR
C7 C 0.154(3) 1.9846(13) 0.1003(14) 0.117(8) Uani 1 d . . .
H7A H 0.1782 2.0383 0.1215 0.175 Uiso 1 calc . . GR
H7B H 0.0647 1.9700 0.1221 0.175 Uiso 1 calc . . GR
H7C H 0.1376 2.0007 0.0492 0.175 Uiso 1 calc . . GR
C4 C 1.024(3) 0.5494(14) 0.2034(12) 0.115(8) Uani 1 d . . .
H4 H 0.9974 0.5573 0.2514 0.139 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl5 2.694(4) . ?
Sb1 Cl7 2.447(4) . ?
Sb1 Cl8 2.443(4) . ?
Sb1 Cl10 2.710(5) . ?
Sb2 Cl3 2.826(4) . ?
Sb2 Cl6 2.457(4) . ?
Sb2 Cl9 2.440(4) . ?
Sb2 Cl11 2.527(4) . ?
Cl1 C30 1.731(17) . ?
Cl2 C38 1.755(16) . ?
N7 C17 1.521(18) . ?
N7 C18 1.486(16) . ?
N7 C23 1.490(17) . ?
N7 C34 1.501(19) . ?
N11 C31 1.42(2) . ?
N11 C32 1.52(2) . ?
N11 C70 1.50(2) . ?
N11 C7 1.47(2) . ?
C12 C20 1.35(2) . ?
C12 C46 1.37(2) . ?
C15 C19 1.34(2) . ?
C15 C42 1.40(2) . ?
C18 C20 1.493(18) . ?
C19 C54 1.37(3) . ?
C19 C70 1.53(2) . ?
C20 C41 1.43(2) . ?
C24 C30 1.43(3) . ?
C24 C41 1.36(2) . ?
C29 C38 1.35(2) . ?
C29 C54 1.35(3) . ?
C30 C46 1.38(3) . ?
C38 C42 1.38(2) . ?
Cl12 C35 1.73(3) . ?
C8 C26 1.35(3) . ?
C8 C44 1.40(3) . ?
N14 C50 1.50(2) . ?
N14 C67 1.52(3) . ?
N14 C76 1.46(2) . ?
N14 C81 1.55(2) . ?
C26 C76 1.55(3) . ?
C26 C4 1.40(3) . ?
C35 C44 1.23(3) . ?
C35 C52 1.41(3) . ?
C52 C4 1.31(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl5 Sb1 Cl10 178.94(14) . . ?
Cl7 Sb1 Cl5 90.07(13) . . ?
Cl7 Sb1 Cl10 89.01(15) . . ?
Cl8 Sb1 Cl5 90.68(14) . . ?
Cl8 Sb1 Cl7 93.27(16) . . ?
Cl8 Sb1 Cl10 88.84(14) . . ?
Cl6 Sb2 Cl3 87.68(13) . . ?
Cl6 Sb2 Cl11 89.56(14) . . ?
Cl9 Sb2 Cl3 90.50(14) . . ?
Cl9 Sb2 Cl6 95.69(15) . . ?
Cl9 Sb2 Cl11 92.02(16) . . ?
Cl11 Sb2 Cl3 176.44(13) . . ?
C18 N7 C17 108.8(11) . . ?
C18 N7 C23 109.8(11) . . ?
C18 N7 C34 112.7(11) . . ?
C23 N7 C17 107.5(11) . . ?
C23 N7 C34 107.9(13) . . ?
C34 N7 C17 110.1(12) . . ?
C31 N11 C32 106.8(15) . . ?
C31 N11 C70 109.5(14) . . ?
C31 N11 C7 107.5(16) . . ?
C70 N11 C32 113.1(13) . . ?
C7 N11 C32 110.3(15) . . ?
C7 N11 C70 109.5(14) . . ?
C20 C12 C46 121.5(17) . . ?
C19 C15 C42 117.8(16) . . ?
N7 C18 C20 116.3(12) . . ?
C15 C19 C54 120.5(17) . . ?
C15 C19 C70 116.8(16) . . ?
C54 C19 C70 122.3(16) . . ?
C12 C20 C18 122.0(15) . . ?
C12 C20 C41 120.4(14) . . ?
C41 C20 C18 117.4(15) . . ?
C41 C24 C30 119.8(16) . . ?
C38 C29 C54 120.6(19) . . ?
C24 C30 Cl1 120.3(15) . . ?
C46 C30 Cl1 120.1(18) . . ?
C46 C30 C24 119.4(16) . . ?
C29 C38 Cl2 119.9(13) . . ?
C29 C38 C42 118.3(16) . . ?
C42 C38 Cl2 120.4(13) . . ?
C24 C41 C20 118.7(16) . . ?
C38 C42 C15 121.0(16) . . ?
C12 C46 C30 119.9(19) . . ?
C29 C54 C19 120.9(19) . . ?
N11 C70 C19 113.6(14) . . ?
C26 C8 C44 120(2) . . ?
C50 N14 C67 111.0(19) . . ?
C50 N14 C81 107.4(17) . . ?
C67 N14 C81 105.3(19) . . ?
C76 N14 C50 115.4(17) . . ?
C76 N14 C67 107.6(18) . . ?
C76 N14 C81 109.7(17) . . ?
C8 C26 C76 124(2) . . ?
C8 C26 C4 112(2) . . ?
C4 C26 C76 123(2) . . ?
C44 C35 Cl12 123(2) . . ?
C44 C35 C52 121(3) . . ?
C52 C35 Cl12 116(2) . . ?
C35 C44 C8 123(3) . . ?
C4 C52 C35 115(2) . . ?
N14 C76 C26 113.9(18) . . ?
C52 C4 C26 127(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HCl'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2112887'
loop_
_audit_author_name
_audit_author_address
'Wang Yan Ning'
;Jiang Su University of Science and Technology
China
;
_audit_update_record             
;
2021-09-29 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(Cl4 Sb), 3(C10 H15 Br N), Cl'
_chemical_formula_sum            'C30 H45 Br3 Cl9 N3 Sb2'
_chemical_formula_weight         1249.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3055(3)
_cell_length_b                   14.9937(6)
_cell_length_c                   18.0441(7)
_cell_angle_alpha                84.989(3)
_cell_angle_beta                 86.538(3)
_cell_angle_gamma                74.258(2)
_cell_volume                     2412.13(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.616
_exptl_absorpt_coefficient_mu    4.127
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29777
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.512
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5709
_reflns_number_total             8475
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         8.026
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8475
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.1008
_refine_ls_restrained_S_all      1.340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3214
_refine_ls_wR_factor_ref         0.3504
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C14(H14A,H14B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C40(H40), C55(H55), C56(H56), C18(H18), C4(H4), C19(H19), C6(H6),
 C9(H9), C16(H16), C11(H11), C22(H22)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C0AA(H0AA,H0AB,H0AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.82368(10) 0.36286(7) 0.31580(5) 0.0627(4) Uani 1 1 d . U . . .
Sb2 Sb 0.70330(10) 0.59618(7) 0.20472(5) 0.0614(4) Uani 1 1 d . U . . .
Cl3 Cl 0.9685(4) 0.5349(2) 0.28489(17) 0.0630(8) Uani 1 1 d . U . . .
Br6 Br 0.6366(3) 0.93202(16) 0.14452(18) 0.1433(10) Uani 1 1 d . U . . .
Br7 Br -0.0077(5) 1.1933(2) 0.01833(16) 0.1596(13) Uani 1 1 d . U . . .
Cl8 Cl 0.7886(5) 0.3896(4) 0.1631(3) 0.0956(14) Uani 1 1 d . U . . .
Cl9 Cl 0.8476(5) 0.6533(4) 0.1020(2) 0.0914(13) Uani 1 1 d . U . . .
Cl10 Cl 0.4715(4) 0.6575(4) 0.1293(2) 0.0901(12) Uani 1 1 d . U . . .
Cl11 Cl 0.6436(5) 0.7398(3) 0.2682(2) 0.0854(11) Uani 1 1 d . U . . .
C10 C 0.4777(16) 1.2514(10) 0.0829(7) 0.067(3) Uani 1 1 d . U . . .
C13 C 0.469(3) 1.1037(14) 0.0667(14) 0.141(10) Uani 1 1 d . U . . .
H13 H 0.4218 1.0646 0.0446 0.169 Uiso 1 1 calc R . . . .
C30 C 0.5806(18) 1.0626(12) 0.1174(9) 0.081(4) Uani 1 1 d . U . . .
C40 C 0.429(2) 1.1902(12) 0.0488(8) 0.089(5) Uani 1 1 d . U . . .
H40 H 0.3610 1.2124 0.0097 0.107 Uiso 1 1 calc R . . . .
C55 C 0.636(2) 1.1159(13) 0.1545(10) 0.095(5) Uani 1 1 d . U . . .
H55 H 0.7099 1.0907 0.1903 0.114 Uiso 1 1 calc R . . . .
C56 C 0.580(2) 1.2152(14) 0.1382(11) 0.101(5) Uani 1 1 d . U . . .
H56 H 0.6132 1.2564 0.1658 0.121 Uiso 1 1 calc R . . . .
Cl1 Cl 0.7001(5) 0.2393(3) 0.3241(2) 0.0876(12) Uani 1 1 d . U . . .
Cl2 Cl 1.0716(4) 0.2530(3) 0.3042(3) 0.0903(12) Uani 1 1 d . U . . .
Cl12 Cl 0.8426(5) 0.3424(5) 0.4634(3) 0.119(2) Uani 1 1 d . U . . .
N14 N 0.2982(14) 1.4037(10) 0.1130(7) 0.081(3) Uani 1 1 d . U . . .
C17 C 0.4302(17) 1.3530(11) 0.0655(9) 0.079(4) Uani 1 1 d . U . . .
H17A H 0.4040 1.3655 0.0126 0.095 Uiso 1 1 calc R . . . .
H17B H 0.5157 1.3787 0.0720 0.095 Uiso 1 1 calc R . . . .
N12 N 0.2936(12) 0.3637(8) 0.4817(6) 0.062(2) Uani 1 1 d . U . . .
C14 C 0.3425(18) 0.2682(11) 0.4520(8) 0.073(3) Uani 1 1 d . U . . .
H14A H 0.2544 0.2565 0.4305 0.087 Uiso 1 1 calc R . . . .
H14B H 0.4164 0.2703 0.4105 0.087 Uiso 1 1 calc R . . . .
C15 C 0.4074(18) 0.1886(12) 0.5031(9) 0.080(3) Uani 1 1 d . U . . .
C1 C 0.4292(19) 0.3877(13) 0.5088(11) 0.095(5) Uani 1 1 d . U . . .
H1A H 0.4687 0.3451 0.5517 0.142 Uiso 1 1 calc GR . . . .
H1B H 0.4000 0.4517 0.5237 0.142 Uiso 1 1 calc GR . . . .
H1C H 0.5063 0.3817 0.4687 0.142 Uiso 1 1 calc GR . . . .
C2 C 0.187(2) 0.3680(13) 0.5457(9) 0.089(4) Uani 1 1 d . U . . .
H2A H 0.0849 0.3932 0.5287 0.134 Uiso 1 1 calc GR . . . .
H2B H 0.2071 0.4082 0.5816 0.134 Uiso 1 1 calc GR . . . .
H2C H 0.1980 0.3053 0.5696 0.134 Uiso 1 1 calc GR . . . .
C18 C 0.5546(19) 0.1638(13) 0.5190(10) 0.092(5) Uani 1 1 d . U . . .
H18 H 0.6178 0.1999 0.4970 0.110 Uiso 1 1 calc R . . . .
C3 C 0.2242(18) 0.4309(11) 0.4235(8) 0.075(4) Uani 1 1 d . U . . .
H3A H 0.2953 0.4303 0.3811 0.113 Uiso 1 1 calc GR . . . .
H3B H 0.1941 0.4929 0.4423 0.113 Uiso 1 1 calc GR . . . .
H3C H 0.1359 0.4150 0.4076 0.113 Uiso 1 1 calc GR . . . .
C4 C 0.378(3) 0.0625(13) 0.5929(13) 0.111(6) Uani 1 1 d . U . . .
H4 H 0.3142 0.0296 0.6193 0.134 Uiso 1 1 calc R . . . .
C19 C 0.323(2) 0.1365(12) 0.5405(11) 0.098(5) Uani 1 1 d . U . . .
H19 H 0.2194 0.1515 0.5302 0.118 Uiso 1 1 calc R . . . .
C20 C 0.1709(18) 1.3635(15) 0.1140(11) 0.102(6) Uani 1 1 d . U . . .
H20A H 0.1568 1.3485 0.0636 0.154 Uiso 1 1 calc GR . . . .
H20B H 0.0804 1.4083 0.1317 0.154 Uiso 1 1 calc GR . . . .
H20C H 0.1903 1.3067 0.1474 0.154 Uiso 1 1 calc GR . . . .
C5 C 0.528(2) 0.0399(11) 0.6044(9) 0.085(4) Uani 1 1 d . U . . .
C6 C 0.616(2) 0.0842(15) 0.5685(12) 0.111(6) Uani 1 1 d . U . . .
H6 H 0.7208 0.0638 0.5750 0.133 Uiso 1 1 calc R . . . .
N1 N 0.1249(15) 0.7910(12) 0.2593(9) 0.099(4) Uani 1 1 d . U . . .
C7 C 0.235(2) 0.8547(15) 0.2344(13) 0.112(5) Uani 1 1 d . U . . .
H7A H 0.2640 0.8777 0.2796 0.134 Uiso 1 1 calc R . . . .
H7B H 0.3271 0.8156 0.2112 0.134 Uiso 1 1 calc R . . . .
C8 C 0.1739(19) 0.9340(15) 0.1828(13) 0.098(4) Uani 1 1 d . U . . .
C9 C 0.083(2) 1.0319(16) 0.2048(11) 0.105(5) Uani 1 1 d . U . . .
H9 H 0.0672 1.0382 0.2569 0.126 Uiso 1 1 calc R . . . .
C16 C 0.197(3) 0.9292(16) 0.1097(13) 0.115(5) Uani 1 1 d . U . . .
H16 H 0.2555 0.8725 0.0916 0.139 Uiso 1 1 calc R . . . .
C11 C 0.026(2) 1.1052(16) 0.1635(12) 0.107(5) Uani 1 1 d . U . . .
H11 H -0.0276 1.1623 0.1826 0.129 Uiso 1 1 calc R . . . .
C21 C 0.090(2) 0.7509(16) 0.1857(11) 0.107(6) Uani 1 1 d . U . . .
H21A H 0.0387 0.8023 0.1512 0.161 Uiso 1 1 calc GR . . . .
H21B H 0.0252 0.7094 0.1985 0.161 Uiso 1 1 calc GR . . . .
H21C H 0.1833 0.7162 0.1620 0.161 Uiso 1 1 calc GR . . . .
C12 C 0.051(3) 1.0935(16) 0.0879(12) 0.124(6) Uani 1 1 d . U . . .
C22 C 0.138(3) 1.0054(17) 0.0567(14) 0.135(7) Uani 1 1 d . U . . .
H22 H 0.1528 0.9999 0.0045 0.163 Uiso 1 1 calc R . . . .
C23 C 0.344(2) 1.400(2) 0.1889(12) 0.132(8) Uani 1 1 d . U . . .
H23A H 0.2999 1.3575 0.2206 0.198 Uiso 1 1 calc GR . . . .
H23B H 0.3107 1.4625 0.2072 0.198 Uiso 1 1 calc GR . . . .
H23C H 0.4535 1.3783 0.1900 0.198 Uiso 1 1 calc GR . . . .
C24 C 0.247(3) 1.5011(14) 0.0809(16) 0.148(8) Uani 1 1 d . U . . .
H24A H 0.2972 1.5399 0.1051 0.222 Uiso 1 1 calc GR . . . .
H24B H 0.1389 1.5241 0.0892 0.222 Uiso 1 1 calc GR . . . .
H24C H 0.2720 1.5035 0.0274 0.222 Uiso 1 1 calc GR . . . .
C25 C -0.032(3) 0.839(2) 0.2877(15) 0.166(10) Uani 1 1 d . U . . .
H25A H -0.0353 0.8356 0.3422 0.249 Uiso 1 1 calc GR . . . .
H25B H -0.1033 0.8084 0.2707 0.249 Uiso 1 1 calc GR . . . .
H25C H -0.0586 0.9044 0.2684 0.249 Uiso 1 1 calc GR . . . .
Cl20 Cl 0.5354(4) 0.5082(3) 0.32191(19) 0.0734(10) Uani 1 1 d . U . . .
Br4 Br 0.6106(4) -0.06375(16) 0.67029(15) 0.1416(11) Uani 1 1 d . U . . .
C0AA C 0.201(3) 0.702(2) 0.3197(15) 0.173(11) Uani 1 1 d . U . . .
H0AA H 0.3003 0.6690 0.3008 0.259 Uiso 1 1 calc GR . . . .
H0AB H 0.1372 0.6587 0.3256 0.259 Uiso 1 1 calc GR . . . .
H0AC H 0.2086 0.7249 0.3679 0.259 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl8 2.775(5) . ?
Sb1 Cl1 2.422(4) . ?
Sb1 Cl2 2.453(4) . ?
Sb1 Cl12 2.666(5) . ?
Sb2 Cl3 2.827(3) . ?
Sb2 Cl9 2.454(4) . ?
Sb2 Cl10 2.531(4) . ?
Sb2 Cl11 2.442(4) . ?
Br6 C30 1.911(17) . ?
Br7 C12 1.85(2) . ?
C10 C40 1.34(2) . ?
C10 C56 1.39(2) . ?
C10 C17 1.48(2) . ?
C13 C30 1.40(2) . ?
C13 C40 1.27(2) . ?
C30 C55 1.31(2) . ?
C55 C56 1.45(3) . ?
N14 C17 1.517(18) . ?
N14 C20 1.467(19) . ?
N14 C23 1.45(2) . ?
N14 C24 1.48(3) . ?
N12 C14 1.515(19) . ?
N12 C1 1.521(17) . ?
N12 C2 1.471(18) . ?
N12 C3 1.441(18) . ?
C14 C15 1.46(2) . ?
C15 C18 1.36(2) . ?
C15 C19 1.37(2) . ?
C18 C6 1.43(3) . ?
C4 C19 1.40(3) . ?
C4 C5 1.37(3) . ?
C5 C6 1.30(3) . ?
C5 Br4 1.886(17) . ?
N1 C7 1.60(3) . ?
N1 C21 1.59(2) . ?
N1 C25 1.52(3) . ?
N1 C0AA 1.67(3) . ?
C7 C8 1.45(3) . ?
C8 C9 1.55(3) . ?
C8 C16 1.33(3) . ?
C9 C11 1.28(3) . ?
C16 C22 1.43(4) . ?
C11 C12 1.39(3) . ?
C12 C22 1.49(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Sb1 Cl8 90.85(12) . . ?
Cl1 Sb1 Cl2 92.22(17) . . ?
Cl1 Sb1 Cl12 88.65(15) . . ?
Cl2 Sb1 Cl8 93.65(14) . . ?
Cl2 Sb1 Cl12 89.32(17) . . ?
Cl12 Sb1 Cl8 177.01(15) . . ?
Cl9 Sb2 Cl3 88.51(12) . . ?
Cl9 Sb2 Cl10 88.83(14) . . ?
Cl10 Sb2 Cl3 177.02(13) . . ?
Cl11 Sb2 Cl3 88.44(12) . . ?
Cl11 Sb2 Cl9 94.58(17) . . ?
Cl11 Sb2 Cl10 90.43(15) . . ?
C40 C10 C56 116.7(15) . . ?
C40 C10 C17 124.3(14) . . ?
C56 C10 C17 119.1(14) . . ?
C40 C13 C30 123.6(18) . . ?
C13 C30 Br6 122.4(13) . . ?
C55 C30 Br6 118.0(13) . . ?
C55 C30 C13 119.1(17) . . ?
C13 C40 C10 122.2(15) . . ?
C30 C55 C56 116.8(16) . . ?
C10 C56 C55 121.2(15) . . ?
C20 N14 C17 112.8(12) . . ?
C20 N14 C24 107.3(18) . . ?
C23 N14 C17 109.1(14) . . ?
C23 N14 C20 108.4(15) . . ?
C23 N14 C24 111.0(17) . . ?
C24 N14 C17 108.2(14) . . ?
C10 C17 N14 114.5(12) . . ?
C14 N12 C1 109.1(12) . . ?
C2 N12 C14 112.5(12) . . ?
C2 N12 C1 106.6(13) . . ?
C3 N12 C14 109.3(10) . . ?
C3 N12 C1 110.7(12) . . ?
C3 N12 C2 108.6(12) . . ?
C15 C14 N12 118.5(11) . . ?
C18 C15 C14 122.3(16) . . ?
C18 C15 C19 115.7(17) . . ?
C19 C15 C14 121.9(15) . . ?
C15 C18 C6 121.1(18) . . ?
C5 C4 C19 117(2) . . ?
C15 C19 C4 124.2(18) . . ?
C4 C5 Br4 118.7(15) . . ?
C6 C5 C4 122.2(18) . . ?
C6 C5 Br4 119.0(15) . . ?
C5 C6 C18 119.7(18) . . ?
C7 N1 C0AA 112.9(15) . . ?
C21 N1 C7 106.6(14) . . ?
C21 N1 C0AA 108.6(18) . . ?
C25 N1 C7 117.6(19) . . ?
C25 N1 C21 101.1(16) . . ?
C25 N1 C0AA 109.1(18) . . ?
C8 C7 N1 115.1(14) . . ?
C7 C8 C9 125.5(19) . . ?
C16 C8 C7 121(2) . . ?
C16 C8 C9 113(2) . . ?
C11 C9 C8 130(2) . . ?
C8 C16 C22 123(2) . . ?
C9 C11 C12 114(2) . . ?
C11 C12 Br7 120.7(18) . . ?
C11 C12 C22 124(2) . . ?
C22 C12 Br7 114.9(17) . . ?
C16 C22 C12 116(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HCl'
